Patent GB-633685-A (GB)
Title: Improvements in or relating to methods of imparting flavour and aroma to food products
IPC: A23L27/00
Filed: 1942-12-23
Abstract: For incorporation with a food there is made a derivative of a flavour and aroma bearing constituent of a volatile oil having in its molecule a =C : O or -OH group by (i) reaction of the =C : O group of the constituent with a -NH2 group of a reagent, (ii) reaction of the -OH group of the constituent with a =C : O group of a reagent, or (iii) reaction of the -OH group of the constituent with a -C(O)O- group of a reagent, the derivative being other than an N-substituted amide, an N-substituted aromatic amino acid or a cyclic ether, and being stable, non-volatile and non-oxidizable under normal conditions of storage, but capable of being decomposed or hydrolysed in the ultimate preparation of the food to reproduce the constituent and leave a residue compatible with the flavour and aroma of the food in which the derivative is incorporated.  Examples of (i) are the production of diacetyl thioureide of m.p. 118-119 DEG  C. by addition of diacetyl to thiourea in ethanol-HCl solution, of diacetyl-di(ethanolamine) of m.p. 121-123 DEG  C. from diacetyl and diethanolamine, of acetylmethyl carbinol-ethanolamine of m.p. 101-102 DEG  C. from acetylmethylcarbinol and ethanolamine, of N-citrylidene-glucosamine of m.p. 139-140 DEG  C. from citral and glucosamine in ethanol and ether, of N-citrylidene-glucose ammonia of m.p. ca. 50 DEG  C. from citral and glucose ammonia in warm methanol, of N-citrylidene-sodium glutamate from an aqueous solution of sodium glutamate, citral and ethanol, of N-benzylidene calcium glycinate by shaking benzaldehyde with an ammoniated aqueous solution of glycine and calcium acetate, of N-cinnamylidene-calcium-glycinate by shaking cinnamic aldehyde with a hot aqueous solution of glycine and calcium hydroxide, of N-isopentylidene-calcium-glutamate from isovaleric aldehyde with an aqueous solution of calcium glutamate, of N-furfurylidene-calcium-glutamate from furfuraldehyde and an aqueous solution of calcium glutamate, of N-cinnamylidene-calcium glutamate by agitation of an alcoholic solution of cassia oil with an aqueous solution of calcium glutamate, and of N-citrylidene-calcium glutamate by agitation of an alcoholic solution of citral with an aqueous solution of calcium glutamate. Examples of (ii) are the production of geranyl hemi-acetal of penta-acetyl-aldehydo-galactose of m.p. 91-92 DEG  C. by precipitation from a solution in warm geraniol of aldehydo-a -galactose-penta-acetate, of citronellyl hemi-acetal of penta-acetyl-aldehydo-galactose of m.p. 102-103 DEG  C. by precipitation from a solution in warm citronellol of aldehydo-a -galactose-penta-acetate, of phenylethyl hemi-acetal of penta-acetyl-aldehydo-galactose of m.p. 103-104 DEG  C. by precipitation from a solution in warm phenylethyl alcohol of aldehydo-penta-acetyl-galactose, of menthyl hemi-acetal of penta-acetyl-aldehydo-galactose of m.p. 89-91 DEG  C. by dissolving equimolecular quantities of menthol and pentaacetyl-aldehydo-galactose in dry benzene containing dry HCl, of phenylethyl hemi-ketal of dimethylalloxan of m.p. 100-102 DEG  C. from phenyl ethyl alcohol and dimethylalloxan in dry acetone, and of decanol hemi-acetal of decanal of m.p. 31 DEG  C. by mixing equimolecular quantities of decanol and decanal.  Examples of (iii) are the production of phenylethylgluconate of m.p. 104-106 DEG  C. by crystallization from a mixture of phenyl ethyl alcohol and glucono-lactone in the presence of dry HCl, of terpinyl-potassium-carbonate by refluxing a solution of terpineol in toluene with metallic sodium and metallic potassium, diluting the solution with dry toluene and ether, and bubbling dry carbon dioxide therethrough until precipitation is complete, of menthyl potassium carbonate by refluxing a solution of menthol in toluene with metallic sodium and potassium, diluting the solution with dry toluene and ether and treating with dry carbon dioxide until precipitation is complete.ALSO:To one or more ingredients of a food is added a derivative made from a flavour and aroma bearing constituent of a volatile oil having in its molecule a carbonyl or hydroxyl group by (i) reaction of the =C : O group of the constituent with a -NH2 group of a reagent, (ii) reaction of the -OH group of the constituent with a =C : O group of a reagent, or (iii) reaction of the -OH group of the constituent with a -C(O)O- group of a reagent, the derivative being other than an N-substituted amide, an N-substituted aromatic amino acid or a cyclic ether, and being stable, non-volatile and non-oxidizable under normal conditions of storage, but capable of being decomposed or hydrolyzed in the ultimate preparation of the food to reproduce the constituent and leave a residue compatible with the flavour and aroma of the prepared food.  Examples of (i) are the production of diacetyl-thioureide from diacetyl and thiourea and of diacetyl-di (ethanolamine) from diacetyl and ethanolamine, for reproducing butter-like flavours and for addition to raspberry, orange or strawberry flavours, and to dried extracts of roasted beverage materials, of acetyl methyl carbinol ethanolamine from acetyl methyl carbinol and ethanolamine for reproducing butter-like flavours, of N-citrylidene-glucosamine, -glucose ammonia, -sodium glutamate, and -calcium glutamate from citral and glucosamine, glucose ammonia, sodium glutamate and calcium glutamate for reproducing lemon or lime flavours, of N-benzylidene calcium glycinate from benzaldehyde, glycine and calcium acetate, of N-cinnamylidene-calcium glycinate from glycine, calcium hydroxide and cinnamic aldehyde for reproducing cinnamon flavour in chicle and gelatin desserts, of N-isopentylidene or N-furfurylidene calcium glutamate from isovaleric aldehyde or furfuraldehyde and calcium glutamate for addition to dried extracts of roasted beverage materials, e.g., coffee extract, and of N-cinnamylidene-calcium glutamate from cinnamic aldehyde or cassia oil and calcium glutamate for absorption in anhydrous glucose or the like to impart a cinnamon flavour to gelatin desserts and the like.  Examples of (ii) are the production of geranyl, citronellyl, or phenyl ethyl hemi-acetals of penta-acetyl-aldehydo-galactose from geraniol, citronellol or phenyl ethyl alcohol and aldehydo-d-galactose penta-acetate or aldehydo-penta-acetyl-galactose, for use in citrus flavours, of menthyl hemi-acetal of penta-acetyl-aldehydo-galactose from menthol and penta-acetyl-aldehydo-galactose for mint flavouring and imparting the cooling sensation of menthol, of phenyl ethyl hemi-ketal of dimethylalloxan from phenyl ethyl alcohol and dimethylalloxan for fruit-flavoured products, and of decanol hemi-acetal of decanal from decanol and decanal for introducing "freshness" into citrus-flavoured foods.  Examples of (iii) are the production of phenylethyl gluconate from phenyl ethyl alcohol and gluconolactone for the regeneration of phenyl ethyl alcohol in acid gelatin desserts, of terpinyl potassium carbonate from terpineol, metallic sodium and potassium, and carbon dioxide for reproducing distilled lime oil flavour, and of menthyl potassium carbonate from menthol, metallic sodium and potassium, and carbon dioxide for mint flavours.